Highly stereoselective synthesis of 2,3- unsaturated thioglycopyranosides employing molecular iodine

Molecular iodine has been utilized for the first time for the thioglycosidation of D-glycals with various thiols to afford the corresponding 2,3-unsaturated thioglycosides in high yields. In the case of tri-O-acetyl-D-glucal, the α-anomer was obtained exclusively. The use of readily available iodine makes this method quite simple, more convenient, and practical

Three-component reaction of a δ-hydroxy-α,β-unsaturated aldehyde with arylamines and 1,3-diketones: a novel synthesis of oxa-aza bicycles

δ-Hydroxy-α,β-unsaturated sugar aldehydes (Perlin aldehydes) undergo smooth coupling with β-enamino ketones and β-enamino esters generated in situ from arylamines and 1,3-dicarbonyl compounds in the presence of 10 mol% InCl<SUB>3</SUB> in acetonitrile at 80°C, to produce oxa-aza-bicycles in good yields with high selectivity

The first examples of cyclizations of a glycal with enamines leading to oxa-aza bicyclononene scaffolds

Glycals undergo smooth coupling with β-enaminoketones and β-enaminoesters generated in situ from 1,3-dicarbonyl compounds and arylamines in the presence of 10 mol % of InCl<SUB>3</SUB> in refluxing dichloroethane to produce oxa-aza bicyclononene scaffolds in excellent yields with high selectivity. The use of InCl<SUB>3</SUB> makes this protocol simple, convenient and easy to scale-up